Tips for Solo Travel.

I’ve gotten so many questions about traveling solo ever since my first trip to Stockholm & Copenhagen at the end of 2o16. At the time I was heartbroken and needed some time and space to get away from the mess that is going through a big breakup, and a solo trip sounded like just what I needed to reset and really start to heal. That trip was truly transformative and got me hooked on regularly taking trips by myself – as much as I love traveling overall, I’ve found that solo travel offers something truly unique that you don’t get in any other travel experience. It creates moments of ultimate, totally selfish freedom, while also serving as a great confidence boost for your independence, and the opportunity for some serious moments of reflection.

I cannot recommend taking a trip by yourself enough, even if it’s just a quick weekend away someplace local. Travel doesn’t always have to be long or extravagant, and even if you’re happily married or have someone you really truly love traveling with, I really believe that solo travel is something that everyone should experience at least once in their lives.

A bit of advice and perspective from my end on some frequently asked about topics (and get ready, this post got a liiiiittle long as I was writing it!):

Where To Go: To maximize my time off work I plan ahead and block off travel dates at the beginning of the year, typically around long weekends or other days when my office is closed so I’m able to maximize my travel time while using as few PTO days as possible. Once I’ve gotten my year all planned out, I go ahead and get those days on the company calendar far in advance so I’m able to manage my workload and work around the vacation time of other people on my team. From there it’s time to start tracking flights – I have a whole post on it but I swear by Google Flights for finding travel inspiration through open ended searches, and also tracking flight prices to specific destinations or for certain flights that would work best with my schedule. One of the best things about traveling alone is not having to coordinate travel schedules with anyone else, making it easy to hop on cheap flight deals and take redeye flights to squeeze in extra time for your travels. At the moment my travel wishlist is basically everywhere, so I’m very open when it comes to travel locations and mostly plan around affordable flights, safety and seasonality depending on when I have the days off planned – for example, my company is closed between Christmas and New Years, I was home in New Jersey for Christmas, and Portugal is one of the warmest places you can travel to in Europe during the winter, so I was able to take a short direct flight to Lisbon for under $600 for that week, and also save a lot of money on accommodations by visiting during the off season.

Safety: Safety is definitely a real concern as a female solo traveler but can easily not be an issue if you do a little homework while planning your travel and just use smart judgement when you’re on your trip. As a general rule of thumb, European cities are really easy and safe for solo travel and the Girls Love Travel Facebook group is an amazing resource for checking in on safety, as well as getting general travel recommendations – the community is super active and full of incredible women who have traveled the world and are great for really candid feedback (for example, I had originally wanted to extend my Portugal trip and head to Morocco and was strongly advised against it for safety reasons). When booking Airbnb accommodations I’ll usually scan reviews for information on the neighborhood around the apartment, looking for mentions of safety and location so I’m able to feel really comfortable staying alone in an apartment. When I’m out and about while traveling solo I make it a point to always be aware of my surroundings, especially at night, avoiding walking around too distracted by my phone or with headphones in, and keeping a close eye on my drinks when out at a bar or restaurant. I’m also a big believer in going with your gut instinct, and really follow this rule when I’m traveling alone – if a street feels a bit sketchy, leave as soon as possible and try to stay in well lit areas after dark, or pop into a hotel/cafe if you have any concern about being followed. Basically my rule is, use your street smarts and don’t be stupid.

Affordability: As I mentioned earlier, finding cheap flights is a big part of what allows me to travel as often as I do. Another secret has been going on shorter trips (like the long weekend I just spent in Mexico City) to cities where you can cram a lot in and really feel like you’ve done a lot in a short amount of time, which will save money on accommodations. I also almost always stay in Airbnb apartments, which is more affordable than hotels and allows you to keep some basic food and drink items stocked to skip eating out for every single meal. While I have yet to stay in a hostel, I know many backpackers and solo travelers swear by them and I’ve seen some pretty luxe and trendy hostels around, so it’s always an option to investigate when planning your trip to save money (and they’re also always the best places to meet other travelers!)

Alone Time: While the non-stop alone time is refreshing at first, it can definitely get a bit lonely if you let yourself overthink it, especially if you’re traveling for an extended period of time. I love reading a ton while traveling and bring both my Kindle with me for reading in my apartments, and sync my books to the Kindle app on my phone for reading on the go – I’ve found the secret to never feeling weird about eating alone in public or the best way to kill a few hours if the weather isn’t great is to grab a cozy spot in a restaurant or cafe and devour a book. You won’t feel alone with the buzz of people around you but you’ll have a distraction to keep you from feeling awkward or burning all of your cell phone data endlessly refreshing social media. I also love walking around a ton which never feels lonely (and helps burn off all of the food you’ll inevitably eat) and often spend hours wandering new cities on foot, turning down any street that looks interesting and popping into random shops and cafes that catch my eye. Not having a plan or someone else’s opinion to consider is such a rare luxury – take full advantage of it!

Lisbon, Portugal

Meeting New People: I’ll be the first to admit that I am not the most warm and friendly person when it comes to strangers – I’m definitely not that girl who you see at the bar and instantly want to walk over and chat with her (I blame a combination of my east coast upbringing + a case of resting bitch face) BUT I have met some really incredible people while traveling over the past few years from all over the world who I still am in contact with regularly. Always go for a bar seat when possible at restaurants and don’t be shy about striking up a conversation with anyone sitting next to you, whether they’re also traveling alone or not (“Where are you from?” is an easy opening line, especially in countries where you overhear someone else speaking English – they’re probably dying to talk to someone!). Being the single lady that I am I also always use Tinder and Bumble when traveling which is a really fun way to meet up with new people and get recommendations for other things to do in the city you’re visiting.

And on the exciting news front, I actually JUST booked my first big solo trip of 2018… like, just a few hours ago! I’ll be spending two weeks in November soaking up some sunshine and exploring Australia – I had actually just blocked the time on my calendar for a big trip covering Thanksgiving + the week before and jumped on the opportunity when I found an amazing deal on flights from the Scott’s Cheap Flights email newsletter (a must for anyone who loves hunting down flight deals; I have the Premium membership and it’s incredible). No real plans yet but I’ll be flying in and out of Sydney and hopping around the country for a bit so if you have any tips or must see’s, send ’em my way 🇦🇺

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Pretty & Fun is a San Francisco lifestyle blog written by Cait Weingartner. It covers fashion, beauty, interior design, and travel and celebrates the little ways to make everyday just a little bit better.
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